I have my 250th episode of Looking Sideways coming up! And I’m also very close to hitting a rather large Substack subscriber milestone, which itself feels like a nicely significant moment.

To mark the big 250, I thought it’d be fun to revisit some favourite articles and podcast episodes from the last eight years of Looking Sideways: continuing with this classic interview with legendary skater Jamie Thomas, originally recorded back in April 2019.

As I discuss in the intro to this episode, for long-term listeners of the show, this chat is one of THE reference points, especially listeners who have been flummoxed by the various left turns I’ve taken with the podcast in the intervening years.

I discussed my thoughts on this, the circumstances around recording this chat, and my thoughts on eight years of Looking Sideways generally, in the new intro I recorded for this Rerun episode.

And with all that in mind it was really interesting to listen back to this one. I think it still stands up! If you’ve not heard this one, have listen and let me know what you think.

Here’s the original intro below:

At some point in their life, every skateboarder chose skating as their ultimate means of self-expression and self-identity. Ask any skater who they are and the chances are the answer will be - I’m a skater. It’s that simple.

So what happens when the one thing that has defined your life no longer serves you in the same way? When the quest you have dedicated your life to no longer fulfils you as it used to? And how do you cope when it has been the defining part of your life in the eyes of the world?

It’s a reckoning that everybody serious about their chosen path has to deal with at some point. For high-level athletes, it is often the most difficult transition of all. And in the skate world, where credibility is defined by your single-minded dedication to the creed of skating, dealing with it publicly is almost unheard of.

Which is why my interview with Jamie Thomas is perhaps the most honest and fascinating episode of the Looking Sideways podcast yet.

For over twenty years, Jamie has been one of the select group of individuals who have defined the culture of skateboarding and changed our understanding of what it means to be a skater. He has been driven by a ferocious work ethic and an unquenchable thirst for progression that have made his career one long continuous run of inspirational successes.

Now, at a critical point in his life, The Chief is looking inward, and bringing that legendary focus and commitment to his own internal struggles.

I’ve been interviewing skaters, snowboarders and surfers for twenty five years now. But I’ve yet to conduct an interview with this level of honesty, or hear a world-renowned figure express their own self-doubt and internal struggles so honestly and so eloquently. I’m grateful to Jamie for trusting me to tell this latest chapter of his story, and for approaching our conversation with such candour and openness. This is The Chief as you’ve never heard him before, tackling the same issues we all have to face at some point with the same honesty and pitiless intensity he brought to one of the most celebrated skate careers of all time.

There are lessons here for all of us - whether you’re skater or not.

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